1. Effect of alkyl chain length in 2-(quinuclidinium)-alkanocarboxylates on structures of their complexes with 2,6-dichloro-4-nitrophenol.
- Author
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Dega-Szafran, Zofia, Olejniczak, Anna, Komasa, Anna, Katrusiak, Andrzej, and Szafran, Mirosław
- Subjects
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NITROPHENOLS , *X-ray diffraction , *NUCLEAR magnetic resonance , *DENSITY functional theory , *FOURIER transform infrared spectroscopy - Abstract
Abstract 2-(Quinuclidinium)-alkanocarboxylates co-crystallize with 2,6-dichloro-4-nitrophenol at the ratios 1:1 and 1:2 depending on the alkyl-chain lengths. The obtained complexes have been characterized by single-crystal X-ray diffraction, UV–vis, FTIR and NMR spectroscopy. The compounds 2-(quinuclidinium)-acetate and 2-(quinuclidinium)-propionate form complexes with 2,6-dichloro-4-nitrophenol at the stoichiometric ratio 1:2, while 2-(quinuclidinium)-butyrate and 2-(quinuclidinium)-valerate at ratio 1:1. Three crystal structures of compounds of these series were determined, but no single crystals of sufficient quality could be obtained of the 2-(quinuclidinium)-butyrate complex. The B3LYP/6-311++G(d,p) approach has been used to determine structures of their isolated molecules and to interpret the IR and UV–vis spectra. Diagrams of the HOMO and LUMO of molecules have been obtained. Graphical abstract Image 1 Highlights • Quiniclidinium-alkanocarboxylates form H B complexes with 2,6-dichloro-4-nitrophenol. • Lower homologues form molecular complexes at the 1:2 ratio. • Longer homologues form proton transfer 1:1 complexes. • Molecular structures were solved by X-ray diffraction and optimized by DFT methods. • UV–vis, FTIR and NMR spectra were measured. [ABSTRACT FROM AUTHOR]
- Published
- 2019
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